Ooh, this question made me wish I had a timeline that gave numbers by year!
Anyway, I think the oldest is probably this one, from 1758, about wanting to rent a house for “five, seven or eleven years” (which seemed funny and arbitrary to me at the time, but apparently it was common for leases to run 5, 7, 11, 15 or 19 years).
This one, from 1785, shows something a little less common: a “wayward’ wife’s lengthy rebuttal to her husband’s notice that she is not to be trusted on his account anymore.
As for the most recent, it’s gotta be this one from 1988 by a long shot. It’s from the Weekly World News and has headlines like “How To Tell If You’re Possessed” and “Rambo Granny Kicks Thug’s Butt”. I don’t usually go much further than 1960, and I usually try to stay before 1950, really, but there was too much here for me to resist.
The second closest would be this one from 1977 which talks about the KKK and American Nazi Party, and how maybe ignoring them and laughing at them just isn’t enough.